iodotrimethyltetrathiafulvalene | 209860-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: iodotrimethyltetrathiafulvalene
• 英文别名: 2-(4,5-Dimethyl-1,3-dithiol-2-ylidene)-4-iodo-5-methyl-1,3-dithiole
• CAS: 209860-66-2
• 化学式: C₉H₉IS₄
• 分子量: 372.339
• InChiKey: BTRRFHICZLGIEN-UHFFFAOYSA-N

物化性质

• 沸点：
  317.714±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.906±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iodotrimethyltetrathiafulvalene 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.5h， 生成 4-ethynyl-4′,5,5′-trimethyltetrathiafulvalene
  参考文献：
  名称：

  四硫富瓦烯-富勒烯体系结构中通过动态桥的门电荷重组率

  摘要：

  开闭案例：人造光合作用系统中电荷分离与重组之间的竞争可以通过使用光致变色动态桥来控制。桥的光致打开和关闭介导了施主（D）和受主（A）之间的电子耦合。

  DOI：

  10.1002/anie.201306183
• 作为产物：
  描述：

  4，4’，5-三甲基四硫富瓦烯 在 lithium diisopropyl amide 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 iodotrimethyltetrathiafulvalene
  参考文献：
  名称：

  四硫富瓦烯-富勒烯体系结构中通过动态桥的门电荷重组率

  摘要：

  开闭案例：人造光合作用系统中电荷分离与重组之间的竞争可以通过使用光致变色动态桥来控制。桥的光致打开和关闭介导了施主（D）和受主（A）之间的电子耦合。

  DOI：

  10.1002/anie.201306183

文献信息

• Molecular Wires Comprising π-Extended Ethynyl- and Butadiynyl-2,5-Diphenyl-1,3,4-Oxadiazole Derivatives:  Synthesis, Redox, Structural, and Optoelectronic Properties
  作者：Changsheng Wang、Lars-Olof Pålsson、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1021/ja0577600

  日期：2006.3.1

  5-Diphenyl-1,3,4-oxadiazole (OXD) derivatives with terminal ethynyl- (4a,b) and butadiynyl- (8a,b) substituents have been synthesized in high yields. 2-Methyl-3,5-hexadiyn-2-ol has not been exploited previously in the synthesis of terminal butadiynes. Crystals of 8a and 8b are remarkably stable to long-term storage under ambient conditions. The X-ray crystal structure of 8a reveals that the butadiyne

  具有末端乙炔基-(4a,b) 和丁二炔基-(8a,b) 取代基的 2,5-二苯基-1,3,4-恶二唑 (OXD) 衍生物已以高产率合成。2-Methyl-3,5-hexadiyn-2-ol 以前没有被用于合成末端丁二炔。8a 和 8b 的晶体在环境条件下对长期储存非常稳定。8a 的 X 射线晶体结构显示丁二炔部分被芳香部分空间隔离，这解释了高稳定性。两个衍生的pi-共轭分子，Donor-(C[triple bond]C)(n)-OXD (n = 1, 2) 和OXD-(C[triple bond]C)(n)-Donor-(C) [三键]C)(n)-OXD (n = 1) [供体 = 四硫富瓦烯 (TTF)、联噻吩、9-(4,5-二甲基-1,3-二硫醇-2-亚基)芴和三苯胺] , 已使用 Sonogashira 反应合成，并通过 X 射线晶体学、循环伏安法和光学吸收/发射光谱进行表征。OXD
• Electronic communication between metal–organic electrophores in an organometallic ruthenium–acetylide–tetrathiafulvalene complex
  作者：Antoine Vacher、Frédéric Barrière、Thierry Roisnel、Dominique Lorcy

  DOI：10.1039/b915158c

  日期：——

  The organic and metal-based electroactive sites in the novel organometallic ruthenium-acetylide-tetrathiafulvalene complex are shown to be strongly electronically coupled.

  新型有机金属钌-乙炔化物-四硫富瓦烯配合物中的有机和金属基电活性位点显示出很强的电子耦合性。
• Electrochromic tetrathiafulvalene derivatives functionalised with 2,5-diaryl-1,3,4-oxadiazole chromophoresElectronic Supplementary Information (ESI) available: spectroelectrochemistry of 3 and 4; 1H-NMR spectra and cyclic voltammograms for 3, 4 and 5; crystallographic information for 5. See http://www.rsc.org/suppdata/cc/b3/b316243p/
  作者：Changsheng Wang、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1039/b316243p

  日期：——

  Electrochromism has been demonstrated by three novel electrochemically-reversible compounds 3, 4 and 5, which were synthesised by Pd catalysed cross-coupling of iodotrimethylTTF (6) and 2,6(7)-diiodoTTF (7) with the 2,5-diaryl-1,3,4-oxadiazole derivatives 1 and 2 containing terminal ethyne and butadiyne groups.

  碘三甲基三联苯（6）和 2,6(7)- 二碘三联苯（7）与含有末端乙炔和丁二烯基团的 2,5- 二芳基-1,3,4-恶二唑衍生物 1 和 2 在钯催化下发生交叉偶联，合成了三种新型电化学可逆化合物 3、4 和 5。
• Ferrocene and Tetrathiafulvalene Redox Interplay across a Bis-acetylide–Ruthenium Bridge
  作者：Antoine Vacher、Frédéric Barrière、Dominique Lorcy

  DOI：10.1021/om400777v

  日期：2013.10.28

  The interplay between two different peripheral electrophores, ferrocene (Fc) and tetrathiafulvalene (TTF), across a bis-acetylide ruthenium organometallic bridge has been studied within the novel complex trans-[Ru(C CMe3TTF) (C CFc)(dppe)(2)] (3) (HC CMe3TTF = 4-ethynyl-4',5,5'-trimethyltetrathiafulvalene). A series of experimental data (electrochemistry, UV-visible spectroelectrochemistry, IR and EPR spectroscopy) and comparison with related complexes from the literature and with the properties of the Fc-C CMe3TTF species (4) have allowed the confident assignment of the electron transfer series in 3 and 4. Cyclic voltammetry experiments in dichloromethane in two supporting electrolytes ([NBu4][PF6] and [Na][B(C6H4(CF3)(2))(4)]) have evidenced the extent of the electrostatic effects on the redox potentials in 3. The results of theoretical calculations (DFT) are consistent with these redox potential assignments but suggest some electronic coupling among the three coupled electrophores, the TTF, the Pc, and the Ru(II) center in 3(center dot+) and 3(2+) and within Fc and TTF in 4(center dot+). Taken together, these data show that the organometallic bis-acetylide ruthenium bridges mediate some appreciable electronic coupling between the two different ferrocene and tetrathiafulvalene electrophores.
• Bis(trimethyltetrathiafulvalenyl) (TriMTTF-TriMTTF)
  作者：Derek E. John、Adrian J. Moore、Martin R. Bryce、Andrei S. Batsanov、Judith A. K. Howard

  DOI：10.1055/s-1998-2087

  日期：1998.6